Top 20 Shadiest SNL Moments

#20: “The White POTUS”

A glossy send-up of HBO’s pitch-dark satire that swaps the resort’s toxic vacationers for a Trump-era inner circle, “The White POTUS” looks, sounds, and moves like prestige TV — then twists the knife with cattiness and casual cruelty. The shade lands on politics, yes, but also on celebrity caricature: SNL cast member Sarah Sherman’s impression of Aimee Lou Wood’s Season 3 character drew heat for exaggerated teeth and a cartoonish accent. Wood called the piece “mean” and “unfunny,” later saying speaking out felt like breaking a personal pattern of tolerating bullying; Sherman apologized privately and publicly. The sketch’s punch isn’t subtle: it’s beautiful people doing ugly things…and enjoying it.

#19: Kristen Wiig Defends Lana Del Rey (& Blasts Her Haters)

Wiig’s breathy “defense” of Lana Del Rey, delivered right after the singer’s shaky live “SNL” moment, is a masterclass in backhanded reassurance. The bit skewers two targets at once: Lana’s deliberately detached persona and the media’s sanctimony. Wiig floats through apologies and self-mythologizing, tossing faux-supportive lines that double as body blows. The comedy is in the tonal dissonance: a porcelain-fragile character calmly cataloging every criticism while calling out the ridiculousness of it all. The segment also shades the internet’s pile-on culture: the way a rough performance becomes a referendum on authenticity. It isn’t rage; it’s frostbite: quiet, delicate, and numbingly cold.

#18: “Complicit”

Scarlett Johansson’s sleek turn as Ivanka is a masterclass in the art of the understatement. The parody ad looks exactly like a luxury spot — creamy lighting, slow-motion filmmaking, hushed VO — then drops a single word like a verdict: Complicit. It’s shade by aesthetic: the gag isn’t that Ivanka is outwardly cruel, it’s that she’s stylish while doing nothing. The punchline is the brand strategy itself: silence, but make it beautiful. The sketch lands because it turns a political critique into a consumer insight. You don’t see the attack coming until the bottle hits the screen… and by then the indictment of passivity in the face of authoritarianism is complete.

#17: “The Californians”

The show’s long-running skewering of L.A. narcissism finds its cruelest edge here. Even a cancer reveal can’t break the characters’ obsession with hair, hallways, and highway routes. The shade isn’t at illness; it’s at people for whom nothing — not intimacy, not grief — can interrupt mirror gazing. The laughter feels guilty, which is why it sticks. The sketch deglamorizes soap-opera melodrama by replacing emotion with freeway directions, exposing a social world where performance has replaced empathy. When tragedy arrives and everyone still asks “Which way did you take?”, the joke crystallizes: vanity is a force field, and it’s suffocating.

#16: “Dateline NBC”

Bill Hader’s Keith Morrison isn’t a hatchet job; it’s a smile with a knife behind it. The grin, the sing-song cadence, the savoring of grisly details — “SNL” shades true-crime TV for treating horror like cozy, vicarious bedtime stories. The craft is in the impression itself: stretched, purring, delighted. The sketch isn’t accusing Morrison of malice; it’s accusing the format of fetish. By turning a dismemberment case into a warm bath of TV tics, the bit drags an entire genre for pretending to be empathetic while chasing goosebumps. It’s ruthlessly specific, drawing on Hader and his colleagues’ genuine admiration for Morrison… and that’s why it felt like the age-old institution of television had been put on notice.

#15: “Justin Bieber for Calvin Klein”

Master impressionist Kate McKinnon’s take on the ubiquitous Canadian pop sensation is the essence of a thirst-trap distilled into a smirk. The parody obliterates a carefully engineered rebrand: black-and-white swagger, micro-tattoos, and underwear-waistband peacocking. The camera loves him; the sketch, however, does not. The shade targets both Bieber and the ad industry’s belief that “grown-up” equals brooding face + fog machine. McKinnon plays the pout as an unshakable habit, and the seduction as a tantrum, revealing the insecurity inside the posturing. It’s a surgical PR deflation that also ribs Calvin Klein himself: if your campaign can be undone by a raised eyebrow and a tummy poke, it probably wasn’t that deep to begin with.

#14: “Matthew McConaughey for Lincoln”

Host and superstar comedian Jim Carrey doesn’t mock the spacey Oscar winner’s obvious talent; he drowns the Lincoln spots in pseudo-Zen vagueness. Whispery philosophy about destiny and leather steering wheels becomes painful self-parody. Inspired by a real-life series of ads McConaughey did for the iconic car brand, the shade hits the luxury-ad ecosystem too: glossy images, non-sequitur wisdom, and brand mystique masquerading as profundity. Carrey’s impression locks onto the musicality of McConaughey’s drawl, then pushes it into absurdity. The kicker is that the sketch didn’t need to exaggerate much to get laughs. That’s the meanest compliment: the original work was already teetering on the edge.

#13: Jeanine Pirro Gets Suspended From Fox News

The outspoken judge and Fox News host has never been one to hold back, and “SNL” has consistently kept that same energy toward her. The Update desk becomes a splash zone as Cecily Strong’s Pirro sloshes, shouts, and blames a suspension on conspirators rather than her own words. The shade is relentless but precise, featuring cadences that turn legalese into barroom monologue; grievance dressed as patriotism; and victimhood performed at full blast. It skewers a media style built on volume over substance — and the gag builds to literal spillage, converting rhetorical excess into physical comedy (at Colin Jost’s expense). Strong later revived the character in 2025, reminding viewers why the bit works: the showboating is the point.

#12: “106 & Park: Top 10 Live”

Two years before his infamous Taylor Swift VMA interruption, SNL staged Kanye as a serial award-show crasher on BET’s “106 & Park.” The bit is almost prophetic: Kenan Thompson and Maya Rudolph’s hosts tee up a montage of Kanye barging into increasingly absurd ceremonies to declare the “real” winner. Shade isn’t just thrown at Kanye’s ego; it’s at the martyr complex that frames self-promotion as a moral crusade. With Kanye in on the joke, he laughed with the show… until life imitated art. When West permanently altered the trajectory of his career in 2009, this sketch played like a cautionary tale nobody heeded.

#11: Kathie Lee Gifford & “Today”

Daytime TV’s loudest brunch hour meets “SNL’s” sharpest knives. The Gifford/Hoda send-ups torch “wine-o’clock” banter, chaotic interviews, and the forced intimacy of morning infotainment. It’s all in the cadence: over-bright, over-familiar, under-prepared. Sketch after sketch, the show mimics a format that sells relatability while smothering substance, exposing how easily sincerity becomes shtick. What keeps it from being pure meanness is the accuracy: you’ve seen these segments. Of course, praise must be heaped upon Kristen Wiig’s boozy Gifford impression. The parodies simply turn the dial from 7 to 10, and the smiles from warm to predatory. It’s friendly TV as jump scare.

#10: Chevy Chase & President Ford

Unlike later “SNL” depictions of U.S. presidents, Chevy Chase didn’t do a voice. In fact, he didn’t do anything to approximate Gerald Ford at all. He didn’t need policy jokes. He just fell down — hard, often, and with commitment — until the pratfall became a president. That’s shade at its purest: a single idea so sticky it rewires public memory. The repetition reads as contempt: Ford isn’t unlucky; Ford is, simply put, a clumsy dope. Decades later, the caricature still trails the late president, who died in 2006. Chase’s quote-unquote “impression” is proof that SNL can brand a politician with one recurring visual.

#9: “President Bill Clinton at McDonald’s”

Phil Hartman’s Clinton, playing on the president’s public image prior to his massive late ‘90s scandals, charms voters while stealing their fries — policy as drive-thru, boundary-less appetite as governing style. The walk-and-talk structure lets Hartman play two things at once: folksy appeal and shameless gluttony. Here, the object of SNL’s ridicule is tactile: crinkled wrappers, greasy fingers, and a candidate who literally won’t stop eating. It’s not a screed about ethics; it’s a demonstration of impulses — how desire leaks into everything. In five minutes, the sketch captures the paradox of Clinton’s political appeal and personal excess better than most biographies. It’s funny, then faintly gross, then weirdly definitive.

#8: “Church Chat: Jim and Tammy Faye Bakker”

As we all know by now, the Church Lady is sanctimony incarnate, and the televangelist scandals were her natural prey. The sketch skewers hypocrisy with a sugar-sweet smile, turning piety into performance art and repentance into a PR strategy. Tammy Faye’s streaked mascara and Jim’s contrition become props for a character who thrives on moral superiority. The shade is theological and theatrical: sin treated as spectacle, forgiveness as optics. Dana Carvey’s sing-song “Well, isn’t that special?” is less a catchphrase than a condemnation: a comedic authority convicting an entire movement of showy righteousness.

#7: Weekend Update: Pete Davidson Roasts GOP Politicians

Davidson’s Update persona is studied nonchalance hiding razor wire. His infamous shot at then-candidate Dan Crenshaw lit up the news cycle, prompting a rare on-air reconciliation the following week. The segment is casual but lethal: tossed-off lines that question character and motive rather than just policy. The controversy also underlined “SNL’s” modern calculus: viral risk tolerated for cultural reach, then clean-up in the second act. The follow-up bit, bringing Crenshaw on to trade jokes, didn’t erase the sting; it simply reframed it as must-see TV. Davidson later publicly recanted his apology to Crenshaw, claiming that he had been pressured into it. As such, the edge — and the lesson — remained.

#6: Mike Myers Tears Elon Musk a New One

Out of nowhere — and then again, and again — Canadian comedy legend and “Wayne’s World” star Mike Myers returned to “SNL” to play Elon Musk as a self-amused chaos engine, specifically in the wake of Musk’s tenure at the Department of Government Efficiency. That was complete with chainsaw props, awkward mannerisms, and shameless Dr. Evil echoes. The impression doesn’t bother flattering genius; it mocks the brand of genius, from cheese-hat stunts to “self-vandalizing Teslas.” In multiple cold opens, Myers’ Musk hijacks scenes to sell nonsense solutions and bask in attention, a parody of disruption that treats incompetence as innovation. The shade works because it’s overqualified: a titan of “SNL” sketchcraft dissecting a titan of tech hype… and enjoying every slice.

#5: “Frank Sinatra & Stevie Wonder Duet”

Joe Piscopo’s volcanic Sinatra and Eddie Murphy’s coolly exasperated Stevie Wonder turn “Ebony and Ivory” into a culture war. Sinatra’s brassy insults and oblivious entitlement crash into Wonder’s restrained dignity; the laughs come from the friction — and from how dated Sinatra’s swagger suddenly feels. It’s not subtle: barbed asides about style, status, and whose music “really” matters. The shade lands as a generational verdict: old-school masculinity swing-dancing on a rug that’s already been pulled. Uncomfortable at times, deliberately so, the sketch is a living argument about respect dressed up as a duet.

#4: “Sean Spicer Press Conference”

Oscar nominee Melissa McCarthy’s take on the brief tenure of the former White House Press Secretary is pure kinetic contempt: gum like gavel, podium as battering ram, facts as chew-toys. The sketch converts a political briefing into slapstick authoritarianism, mocking both the temper and the shamelessness of spin. What makes it devastating is how literal and absurd it feels: the prop podium simply acts out what the words are doing — running people over. The performance reportedly rattled the real Spicer and delighted an audience hungry to see power humbled. It also set a modern template: when press briefings become theater, the rebuttal will be louder theater.

#3: “Sarah Palin & Hillary Clinton Cold Open”

In one of the storied sketch show’s most iconic moments, Tina Fey and Amy Poehler deliver a two-front roast that stuck to both targets. Fey’s Palin is blithe confidence without depth; Poehler’s Hillary is competence curdled into clenched ambition. The script plays like a split-screen verdict on political branding: unearned charisma vs. earned resentment. The sketch itself mattered because it traveled: lines and attitudes bled into mainstream coverage and public memory, overshadowing the real Palin interviews that inspired it. Fey’s Palin remains possibly “SNL’s” best-known and most beloved political impression, owing in no small part to its healthy heaping of shade.

#2: Any Sketch With Alec Baldwin as President Trump

This wasn’t a cameo; it was a siege. Baldwin’s take on Donald Trump — sniffly, pouty, and self-enchanted — turned weekly politics into a running farce. The impression routinely popped up on the news cycle, to the point where a Dominican newspaper once ran a Baldwin photo as if it were the real president. Trump’s public fury, and well-documented distaste for the Emmy winner’s impression, only amplified the bit’s reach. Love or hate the portrayal, it took up space in the public square and refused to leave, a form of shade that became canonized. The key to the gag’s long-running shelf life is its unsparing judgment: a presidency reduced to caricature.

#1: Norm Macdonald vs. O. J. Simpson (& NBC)

No euphemisms, no hedging. On Update, Norm simply decided: O. J. did it — then he wrote jokes like he believed the audience deserved honesty. The relentlessness became the bit, and the bit became legend. It also cost him greatly: NBC executive Don Ohlmeyer, a friend to the disgraced athlete and media personality, removed him from Update mid-season, reportedly as a form of retribution. That’s shade as a moral stance: risking your job to keep the joke brutally on message. In hindsight, it reads less as cruelty than clarity, which is why those deadpan punchlines still circulate every time the case resurfaces. Macdonald’s comedy aged into an eerily prescient public record.

Did we miss any of “SNL’s” shadiest moments? Be sure to tell us in the comments below, because who knows — your suggestion could be featured in a future video!